It has been a busy few days between OGR work and flying a few corporate clients to various destinations, but I finally have a moment to respond to this question.
The answers below are based upon my own experience running the various engines that I have had the pleasure to run over the years.
BEST RIDING STEAM LOCOMOTIVE
Without a doubt, Milwaukee Road 4-8-4 No. 261. When we leased this locomotive to run the New River trips in 1994, I was immediately impressed with the riding qualities of this locomotive. Compared to the 765 of 1993 (see below) she rode like a Cadillac! Because the 261 has an all-weather cab she was a little warmer inside than other locomotives I've run, but all things considered, running the 261 was a very pleasant experience.
SECOND BEST RIDING LOCOMOTIVE
NKP 765. Several of our crew have commented that the post-overhaul 765 rides better than the crew car! With the running gear all back to blueprint specs, the ride is pretty nice now.
WORST RIDING STEAM LOCOMOTIVE
No question - PM 1225. I rode that engine a couple of times 1991 when we double-headed with her. At speed it vibrated so badly that the radio mount broke and a handrail broke - all from the violent shaking that was going on. The vibration was so bad, there were times when I couldn't read the air gauges! Those issues have been fixed and I hear she rides quite nicely now, although I have not been in the engine for many years.
SECOND WORST RIDING STEAM LOCOMOTIVE(S)
It's a tie between BC&G 2-8-0 #13 from the Ohio Central and the pre-overhaul NKP 765 of the early 90's.
I ran the 13 only a couple of times on the Ohio Central for various events, and she was one rough-riding son of a gun. Lots of hard bumps and cab movement all around. Of course, it's an older locomotive with no trailing truck, so that had a lot to do with it.
The 765 of the early 90's was also a rough ride, but in a different way. In that era, the 765's drive wheels were out of balance due to material having leached out of the counterweights over the years. At anything over about 25 mph, the locomotive bounced vertically in rhythm to the rotation speed of the drivers. At 50 mph it was almost unbearable! After a few hours with the locomotive beating up on me like that, I was absolutely beat! Today - with ROUND WHEELS AGAIN - she too rides like a Cadillac, almost as good as the 261.
I have never had the opportunity to ride the cab of the 4449, so I can only imagine what that high-speed run on rough track must have been like!